Pineapple Upside Down Cheesecake

The sliced open pineapple cheesecake on a cake platter, topped with caramelized pineapple, whipped cream, and cherries.

4.75 from 4 votes

Pineapple Upside Down Cheesecake

Pineapple Upside Down Cheesecake tastes like a classic Pineapple Upside Down Cake in cheesecake form! Ultra creamy brown sugar cheesecake is baked atop a crisp graham cracker crust, and filled with a layer of caramelized pineapple filling. Top this stunning dessert with more caramelized pineapple compote, swirls of vanilla whipped cream, and maraschino cherries.

Prep Time1

Cook Time1 45

Cooling & Chilling9

Total Time11 45

Course: Dessert

Cuisine: American

Keyword: Cheesecake, Pineapple, Piña Colada

Servings: + slices

Author: Stephanie Simmons

Ingredients

Pineapple Compote

6 cups pineapple rings, quartered, with juice drained & reserved This equates to 3 cans of pineapple rings - see note #1 below. 1074 grams of pineapple
2/3 cup + 1 tbsp dark brown sugar, packed 158 grams
1 and 1/4 cups pineapple juice
2 tbsp + 1 tsp corn starch
2 tbsp + 1 tsp water
2 tsp vanilla extract
2-3 tbsp vanilla rum or coconut rum optional

For the Crust:

3 cups graham cracker crumbs 276 grams
1/2 cup salted butter, melted 113 grams

For the Cheesecake Batter

32 ounces full fat cream cheese, softened at room temperature 906 grams
1 and 1/2 cups brown sugar 330 grams
4 large eggs, at room temperature
3/4 cup full fat sour cream, at room temperature 180 grams
2 tsp vanilla extract

For the Whipped Cream

4 tsp cold water
1 tsp plain powdered gelatin This is available in the baking aisle of most grocery stores
1 cup heavy whipping cream
1/4 cup + 2 tbsp powdered sugar
2 tsp vanilla extract

For Decorating:

maraschino cherries

US Customary - Metric

Instructions

Make Pineapple Filling/Topping: Stir together the corn starch and water in a small bowl until dissolved, and set nearby.
Add the quartered pineapple chunks, brown sugar, and pineapple juice to a large saucepan. Stir to combine everything. Heat over high heat, with the lid on to speed things up, for 18-25 minutes, stirring occasionally. You want the liquid to reduce a great deal (see photos above). Once the liquid has reduced down to an almost syrupy consistency, reduce the heat to medium high and add the corn starch slurry (stir it again to make sure it's still dissolved). Cook for 1-2 minutes more, stirring, just until the remaining juices have thickened enough to coat the back of a spoon - if you drag your finger through the mixture on the back of a spoon, it should hold a trail. Again, see photos above for reference. Remove from the heat and stir in the vanilla and rum if using. Immediately transfer to a large rimmed baking sheet or something similar to allow the filling to cool quickly in the fridge. It needs to be cooled before using later!
Make-Ahead Tip: Once cooled, store filling in an airtight container until ready to use. This can be done 2-3 days ahead.
6 cups pineapple rings, quartered, with juice drained & reserved, 1 and 1/4 cups pineapple juice, 2 tbsp + 1 tsp corn starch, 2 tbsp + 1 tsp water, 2 tsp vanilla extract , 2-3 tbsp vanilla rum or coconut rum
Make the Crust: Preheat oven to 350° F. Spray a 9-inch springform pan with nonstick spray and place a piece of parchment paper over the bottom, before making sure it's securely fastened. Spray the inside of the pan with nonstick spray.
Melt butter and stir it into the graham crumbs. Press the crust mixture into the bottom of the springform pan and up the sides (see photos above). Bake this for 10 minutes. Set aside. Keep the oven on at 350. Fill a large pot with water and set it on your stove, and get out a large roasting pan – you'll need this for your water bath later.
3 cups graham cracker crumbs, 1/2 cup salted butter, melted
Make the Cheesecake Filling: Remember that your cold ingredients need to come to room temp before you start. In a large mixing bowl, beat the softened cream cheese with electric mixer until creamy, about 1-2 minutes. Add the sugar & mix on high speed until well incorporated, about 1-2 minutes. Scrape the sides of the bowl with a rubber spatula between each step - little lumps of cream cheese love to hide in the bottom of the bowl. Add the eggs one at a time, mixing on medium speed after each until just incorporated. Add the vanilla, sour cream, and rum if using, and mix on medium low speed until just incorporated.
Tip: You can also do this in a stand mixer fitted with the paddle attachment.
32 ounces full fat cream cheese, softened at room temperature , 1 and 1/2 cups brown sugar, 4 large eggs, at room temperature , 3/4 cup full fat sour cream, at room temperature , 2 tsp vanilla extract , 4 tsp cold water
Prepare the Water Bath: Bring the large pot of water to a boil. Get your roasting pan out and place the springform pan with the crust inside of a 10-inch cake pan (or similar size pan that it can evenly sit inside of, while it sits in the roasting pan).
Assemble Cheesecake for Baking: Pour half the cheesecake batter into the springform pan. Spoon about 1/3 of the pineapple filling in an even layer over the batter. Pour the remaining batter on top, and gently smooth it out.
Place your roasting pan on an oven rack positioned in the center of your oven. Set the springform pan nestled in the 10-inch pan inside of the roasting pan. Then, pour the boiling water into the roasting pan only, until you have water about 2 inches deep. (The 10-inch pan is your failsafe buffer against leaks!)
Bake: Bake the cheesecake for 1 hour and 25 minutes to 1 hour and 45 minutes. When done, the cheesecake will have only a slight wobble in the center, and a knife inserted into the edge will come out clean, and will have just a bit of thick batter when inserted into the center. Turn off the oven and crack the door open. Let the cheesecake cool in the oven for 1 hour before removing it.
Cheesecake Cooling: Once the hour is up, remove the pan from the oven. It should be cool enough to handle. Take the springform pan out of the 10-inch pan and set it on a wire rack. Let cool until just slightly warm or room temperature, then cover with foil and refrigerate at least 6 hours or up to 1 day before removing from the pan and serving.
Make the Whipped Cream: Add the water to a small bowl, and sprinkle the gelatin on top. Let sit for 4 minutes, then microwave for 5 seconds to liquify it. Keep nearby.
Add the whipped cream ingredients to a medium bowl and beat on high speed until it begins to thicken. Then, slowly drizzle in the gelatin liquid while you run the mixer on medium speed. Continue mixing on medium high speed until stiff peaks form. Your whipped cream is stabillized and is immediately ready to be piped!
Tip: If you moved a bit slowly and your gelatin has re-solidified, just microwave it for another 3-5 seconds.
1 tsp plain powdered gelatin, 1 cup heavy whipping cream, 1/4 cup + 2 tbsp powdered sugar , 2 tsp vanilla extract
Serve & Store: When ready to serve, release the cheesecake from the springform pan, and place it on a serving plate. Top the cheesecake with pineapple topping, and pipe on the whipped cream (I used a wilton 4B tip). Add maraschino cherries for garnish, then slice and enjoy! Store leftovers in an airtight container in the fridge for 3-4 days.
maraschino cherries

Notes

Note 1: For the pineapple, it's easier to use canned here in my opinion. However, you can use fresh as well. Make sure they're ripe! You'll need three, 20-ounce cans of pineapple rings or three large ripe pineapples (see note below if you need help with this).

Ripe Pineapples: Ripe pineapples should feel firm but not rock hard, and not soft. They should be turning yellow on the outside, and you should smell a ripe pineapple aroma when you sniff the base of the pineapple. You should also be able to pluck one of the leaves without too much effort when ripe.

For more tips and additional info, pleas be sure to read the blog post above! There is a table of contents at the beginning of the post to help you navigate to various topics.

Nutrition